Overthinking Everything So You Don’t Have To

A how-to listicle for aspiring overthinkers

9 min. read

I have a confession to make: I’m an Overthinker.

I think I’ve always been this way, but my condition has worsened with age. And my chosen profession didn’t help.

I overthink as a matter of work, often. And I always overthink my work. Not just the things I make themselves, but how to describe what I do, and what unites it all.

Lately, I’ve come to think that the best way to describe my job is “overthinking everything so you don’t have to.” That’s no surprise, I’m sure, if you’ve popped around this site, or read my books, or seen anything else I’ve made.

But, ironically, I’m also driven, fundamentally, to empower people to _not _need me, via my work. I always endeavor to remove myself from the picture. Making myself irrelevant is one of my primary goals in everything I make, and it’s often the question that leads to the improvements or further work: “How can I create something that is freely available to prevent a person from needing to hire me to do it?”

That’s why, for example, I released my copyright on my work back in 2013: I didn’t want people to have to keep asking me to use it, license it, or reprint it. I removed myself from the middle.

So this creates a bit of a conundrum. No surprise: me finding a conundrum. That’s Overthinking 101.

Recently, I’ve been [over-]thinking about that conundrum a lot. And I’ve felt a growing urge to reconcile it, which brings us here. To the how-to I never suspected I would write: A list of ways that I overthink everything, for those of you who want to DIY (OIY?).

Following is the process I generally follow as I overthink everything in my life and work.

I apply it to everything I create, to the social justice and human rights advocacy I engage in, to how I organize and operate on a “business” level, and even to how I do things in my “personal” life (relationships, puppy training, cooking, etc.).

This is the not-so-secret sauce.

But I suggest you proceed with caution. Overthinking is addictive. I wonder why that is.

Ask yourself “If I wasn’t me, how would I think differently about this?”

The “me” here can stand in for a particular skill, role, social identity, history, disposition, or current attitude you hold. Bonus points if you run the experiment for every one of those dimensions.

The “this” can be anything: an action you’re considering, a value or moral you’re investigating, a social convention, a disagreement you’re having, or anything else that’s on your mind.

Consider whatever you’re thinking about in a bunch of different ways by walking in as many pairs of shoes as possible. Maybe you think about someone you know (e.g., “How would my best friend think about this?”). Or a broad group of people (e.g., “Republicans” if you’re not one). Some of the best overthinking insights come from outlandishly polarized pairs of shoes:

  • What would a person who hates this, hates me, and hates everything I stand for think about this?
  • If an alien appeared in my living room right now, and they were telepathic, and I explained this to them, what might they say (think)?
  • How might a person who doesn’t give a shit about literally _any _social conventions think about this? (If that’s you, think “how might a person who religiously adheres to social convention think about it?”)

These prompts can be thought of as radical experiments in empathy. You’re not going to _know _how those different people might think, but you’ll quickly expand your previous perspective.

And if you’re a competitive overthinker, add “Why?” to the end of each of those. Actually…

Go (at least) three “Why?”s deep.

The reason* toddlers are adults’ Kryptonite is because they’re just old enough to start to understand how things work, but not old enough to have learned that they’re not supposed to question how things work. And in that magical in-between one question reigns supreme: Why?

(*Or maybe that’s not _the _reason. Just _a _reason. But maybe it’s at the core. Hm… I’m not sure. Let’s think about that later.)

I’m sure I don’t need to explain this meme to you, but if you’re never encountered a “Why?”-asking toddler, this clip sums it up beautifully.

Ask yourself “Why?” to anything you’re overthinking, and do your best to answer. The trick here is sincerity. Be like the toddler. You need to genuinely wonder, and truly want to know the core answer, what’s at the bottom of this.

Then do the same thing to whatever answer you come up with. Then do it again.

If you can’t come up with an answer, you’re either (A) not trying hard enough; (B) out of your field of knowledge/expertise; or, if you’ve ruled those two out, © at the true bottom of the quandary.

If C, great! You’ve won this round of overthinking. Kudos, comrade.

If B, phone a friend! Google, YouTube, or Khan Academy can all substitute real friends, if you don’t have any or suspect none of your friends will care about this. But a real person is better for this, because every question they answer will likely beget more questions.

If A, think about the reason why you’re not trying hard enough. That’s often the most interesting “Why?” of them all.

And if you think I’m joking, you’ve sincerely underestimated my overthinking problem.

Brainstorm a list of terrible alternatives.

Sometimes, when we think there’s only one way to think about something, it’s because we’re limiting ourselves to only the “good” or “acceptable” options. Take those guard rails off, and a world of possibilities opens up.

Instead of overthinking something by trying to come up with better, or more accurate, or more helpful, or whatever-positive-related-trait; consider the dumbest, stupidest, least helpful, or just plain painful angles instead.

And come up with as many of them as you can think of.

Bonus points if you think through the list, and for each item on it ask yourself “For whom would this terrible alternative actually be ideal?”

Or “Why might I be thinking of that alternative as terrible?”

Not sure how to answer that? Maybe an unconscious bias is to blame.

Consciously consider unconscious biases.

We like to think of ourselves as rational people (how’s that for a tautology?), but for every thought we are aware of, there’s a team of puppeteers behind the scenes pulling the strings. They’re referred to by the fancy folk as “cognitive biases.”

Even if that’s a new phrase for you, I bet you’re familiar with the concept.

For example, if your parent ever said to you, “If everyone jumped off a bridge, would you?” they were addressing a cognitive bias they suspected was influencing your behavior.

I the above case, the bias is called “Bandwagon Effect.” What a perfect name for that, right?

What’s fun for us overthinkers is that other overthinkers have, for the betterment of us all, clocked countless hours researching and naming hundreds of cognitive biases.

Our reflex might be to label cognitive biases as the enemy to overthinking. But upon second thought (heh) — and as soon as you consciously consider them — they’re actually our greatest ally.

If you’re an overthinker like me, you are probably seeing that list as dozens and dozens of new ways to think about everything.

Here are a few of my go-to cognitive biases that I tend to apply to every situation I overthink, and the question I ask myself:

  • Confirmation bias: “In what ways am I only seeing what I expect or want to see?”
  • Dunning-Kruger Effect: “How might my ignorance about this be making me over confident?”
  • Loss Aversion: “Am I focusing too much on what might be lost, and not enough on what might be gained?”
  • Fundamental Attribution Error: “How might I blaming the people, or symptoms, instead of the situation, or disease?”

(You’ll probably see those biases behind the big steps above. What is “Why?” if not a quest for fundamental attribution? And what is “if I wasn’t me” but a recognition, and subversion, of confirmation bias? If you noticed that before I pointed it out, I’m impressed. You’ve overthought even me. I didn’t notice it until I was editing, at which case I wrote this paragraph.)

But don’t limit yourselves to these. Peruse the list. Or refer to this beautiful graphic that displays a bunch of cognitive biases algorithmically.

Bonus points if you combine a few. For example, “How might confirmation bias and loss aversion combine to be pushing me in favor of the status quo, or doing nothing?”

Every cognitive bias can be the source of a series of questions you ponder to pick apart any situation. In that way, there’s enough fodder there to keep you busy — even with the most trivial of overthinking — for years.

“Should I wear a nice outfit to this party? Or my pajamas?” See you in 2022 with a thoroughly overthought answer.

Oh, wait. Maybe that’s not the best use of our brains. Oh no! I didn’t start with the first step.

But first, always, identify overthinking alternatives

Whatever you’re overthinking — a decision, an action, a value, a social expectation — popped into your mind somehow. You didn’t choose it. There’s no point in overthinking something until you’ve decided, as much as you can, that it’s the right thing to overthink.

So, that’s step one of The Overthinker’s Operations Formula (OOF): overthink thinking about this particular thing. Or, to put it another way, think about all the other things related to this that might be worth overthinking instead.

Does it seem like the only choice you have to make? The only action worth investigating? The only value on the table? Ha! Never.

There are always other options. Always. If you’re struggling to come up with some, start back at the beginning of this article:

  • What might someone prioritize overthinking, instead of the thing you’re about to overthink?
  • Why is this thing worth overthinking? K. Why’s that? Oh. Why?
  • What are a bunch of other comparable things _not _worth overthinking?
  • What biases might be leading you to think that this thing is worth overthinking?

And here’s a new one to add to the list above:

Is there something I’m avoiding doing by overthinking this?

Uh oh. This just got personal. Do you feel attacked? I do. Why am I attacking myself with this article?

This is the most important dilemma an overthinker must face: is overthinking helpful right now, or just procrastination and fear and resistance.

Sometimes the answer is “yes.”

Sometimes overthinking now can save you countless hours of unhelpful doing. Measure twice, cut once. A stitch in time saves nine. And other aphorisms.

But, for us overthinkers, it’s often “no.”

And sometimes we only notice that 1800 words later. Oof.

Featured photo by Sarah Dorweiler on Unsplash. And it’s not a cat navel-gazing, like I initially thought. It’s a cat staring at a tiny mouse toy. Eyes on the prize. Maybe there’s something Rorschachian about that. I’m probably overthinking it.